Discussed: Starting a Startup as a Side Project; Interviewing; Working at Dropbox; Being a Female Founder; Leah’s Favorite Podcasts.

Craig: What does your company do?

Leah:Breaker is an end-to-end podcasting company. Right now we’re building an iOS app for listening to podcasts focused on social discovery. In other words you can see what’s popular amongst the folks you follow and the users of the app.

Craig: What did you do before YC?

Leah: I was an engineer at Dropbox. I worked on engineering product design operations. Basically handling engineering productivity and happiness throughout the lifecycle of an engineer. Stuff like onboarding, growth, and keeping engineers informed and engaged. For me that meant working on the platform for our internal tools–our corporate directory and our seating charts.

Craig: How long were you there?

Leah: Three years. I started as a developer advocate then switched to internal tools.

Craig: How did you end up a Dropbox?

Leah: I actually came across Dropbox at a career fair. I was looking for a job and they were there. I didn’t know if I would be a good fit because I’m not a scalability or performance engineer. I’m more of a product engineer. They had me interview with a couple people on the API team and I love the API team so it ended up being a great fit.

Craig: Why did you decide to leave?

Leah: So I started working on Breaker as a side project. My cofounder Erik Michaels-Ober and I worked on it for about nine months as a side project actually. Before we interviewed at YC we quit our day jobs and decided to either do YC or make it happen another way. We had a prototype and user feedback by the time we quit our jobs. This was different from past startups, where I quit my job before starting to work on the product

Craig: And what did you do before Dropbox?

Leah: I did YC W11 with Convore, which was group, topic-based chat. We pivoted that to Grove, which was kind of like Slack. Eventually we wound that down and I started working at Sincerely as an iOS developer. Then I spent three months contracting at Medium then I had a break then joined Dropbox.

I actually talked to about 30 companies before choosing Dropbox. I did 8 or 9 in-person interviews. I really wanted to see what was out there.

Craig: Whoa. What did you learn from interviewing at so many places?

Leah: Because I was exploring so many options, I was interviewing them just as much as they were interviewing me. I wanted to be open to different types of companies and see where it went. It was actually pretty surprising. There were famous, well-known companies that I thought I would love working for but when I went in for the interview I was realized I definitely didn’t want to work there. The day-to-day wasn’t what I wanted.

Craig: How did you suss that out in the interview?

Leah: The first thing was the people. Who was I interviewing with? Did I respect them and their work? Did I want to get to know them more? A lot of it was the company itself–corporate policies, the office layout. And then lots of little things. What’s the temperature of the office? Do they have plants? All those things that you wouldn’t think really matter but affect your day-to-day life in a big way. So yeah, I was looking for a comfortable, fun work environment and top notch people.

Craig: So you’re one of an increasing number of people that have done YC twice. What are the differences between W17 and W11?

Leah: The weekly dinners and talks are pretty similar. The group structure is different. We have four groups now and there used to be one big group so there were no group partners. The group partners have been a huge improvement. Tim [Brady] and Dalton [Caldwell] have been invaluable as a resource to call upon quickly and reliably. We don’t talk to them every day but definitely more than once a week, which is different than last time.

Craig: What made you want to do YC a second time?

Leah: Erik hadn’t done YC before and really wanted the experience. For me, I felt like I wanted YC to be part of any success I had in the future. I was so grateful for them the first time and it was such a huge help both times. I’m happy to give YC and the partners ownership in anything I do because when I become successful I want YC to be part of it.

Craig: Why did you decide to work on a podcasting app?

Leah: I love building new products but when I’m starting something new I like to know that it’s valuable–to me personally or, more importantly, as a product. Everyone asked me after my first two companies if I was going to start another and my answer was always “no”. It’s so stressful and so much work. But I had a condition that if I found a space which could be greatly improved and I had an amazing team, then I’d try again.

I started listening to podcasts when I was running. I was kind of happy with the existing players but I was having a hard time with discovery. I didn’t find the existing directories of podcast to be particularly relevant to me. So I reached out to Erik who had mentioned a year or so before to reach out if I was looking to start another company. My email to him was about one sentence, “What do you think of podcasts?”, and his reply was pages long. He had been working at Soundcloud and was more into talk audio than the streaming music, and had a lot of ideas.

Craig: What’s it like being a female founder at YC?

Leah: Surprisingly not too different from being a male founder. YC has a large number of female founders. Even in 2011. I’m always pleasantly surprised with that, especially the number of technical female founders. I think YC does a good job of being welcoming and very open to female founders.

Craig: Do you have thoughts on how the industry could be better for female founders?

Leah: I mostly stay out of this discussion because I don’t have solutions. As an engineer I always try to find solutions to problems and I don’t feel like this has an obvious or easy solution. That said, I do encourage female engineers and founders to apply to YC. I often tell them to do it because how they think of YC in their head and what it actually is are usually two different things. The founders in YC are quite diverse. They’re not all American. They’re not all young, white men. It’s a bigger mix than maybe you’d believe.

Craig: On that point, are there other perception vs reality differences with YC that are apparent to you?

Leah: Some people think YC is full-time in the sense you have to live at YC. [Laughter] That’s totally not the case. YC likes you to live near YC but you don’t live at PG and Jessica’s house.

Craig: Any advice for people working at big companies that are thinking about starting a startup?

Leah: Do what we did! Build things on the side. Honestly mostly build Breaker on Sundays. We iterated on the product for months before leaving our jobs. You don’t have to quit your job to do a startup. I think it’s actually better to explore when you have that safety net.

Our initial direction wasn’t the direction we ended up going in. I was interested in building tools for podcasters. Then when we started to talking to podcasters we realized that podcasters just want listeners and data about those listeners. Just providing good tools didn’t really solve that problem. So we shifted focus to work on the user app first. That change in strategy would have been much more painful if we had quit our day jobs to learn it.

Craig: What made you decide to go all in?

Leah: Those choices are always a gradient for me. I’ve had other projects where I’m just not that motivated to finish it or keep going. And I think that’s ok. Many people think of that as a failure but for me it’s ok. If you’re feeling lukewarm about something there’s probably a reason why. Maybe something you’ve learned has changed your perception.

What was nice about Breaker is that I think Erik and I both felt that there was something there. We both kept motivated with day jobs, which said something about the space and the ideas. That made it easier to commit. And having some early users helped us keep going, too.

Craig: What advice would you give yourself when you were just starting out?

Leah: So right out of college I moved to SF. At the time I was very lonely. I didn’t know anyone here. Knowing that I would reestablish myself eventually would have been very comforting. That’s not really startup advice though…

Craig: I think that’s great advice for doing anything new though.

Leah: Yeah. It will be comfortable eventually. It’s uncomfortable now because it’s not familiar but it’ll get easier.

Craig: What are your favorite podcasts right now?

Leah:Missing Richard Simmons: E01 – This is kind of hot right now for all of Breaker. It’s a new serialized mystery show. It’s about what happened to the 80s exercise guru, Richard Simmons. He disappeared from the public eye and has been out of touch with his friends and family and nobody knows why.. It’s sort of like Serial… but I hope no one gets murdered! Ep: 1

Here To Make Friends: S21E09 – It’s Slate’s Bachelor recap show. The hosts discuss this week’s episode with insight from previous contestants and some backstory about The Bachelor. They know a little more about the show than the average viewer.

The Twenty Minute VC: Using Valuations As A Litmus Test – They’re short interviews with VCs. The episodes are on a variety of different topics related to VC and tech.